dihydroartemisinic acid (CHEBI:144078)

ChEBI > Main

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	dihydroartemisinic acid

ChEBI ID	CHEBI:144078

Definition	A monocarboxylic acid that is propanoic acid substituted at position 2 by a (1S,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl group. It is a sesquiterpenoid precursor of the antimalarial drug, artemisinin.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C15H24O2

Net Charge

Average Mass

236.355

Monoisotopic Mass

236.17763

InChI

InChI=1S/C15H24O2/c1-9-4-6-12-10(2)5-7-13(14(12)8-9)11(3)15(16)17/h8,10-14H,4-7H2,1-3H3,(H,16,17)/t10-,11-,12+,13+,14+/m1/s1

InChIKey

JYGAZEJXUVDYHI-DGTMBMJNSA-N

SMILES

[C@@]12(CCC(=C[C@@]2([C@@](CC[C@H]1C)([C@@H](C)C(O)=O)[H])[H])C)[H]

Metabolite of Species	Details
Artemisia annua (NCBI:txid35608)	Identified in petals and leaves. See: DOI

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

ChEBI Ontology
Outgoing	dihydroartemisinic acid (CHEBI:144078) has role plant metabolite (CHEBI:76924) dihydroartemisinic acid (CHEBI:144078) is a carbobicyclic compound (CHEBI:36785) dihydroartemisinic acid (CHEBI:144078) is a monocarboxylic acid (CHEBI:25384) dihydroartemisinic acid (CHEBI:144078) is a octahydronaphthalenes (CHEBI:138397) dihydroartemisinic acid (CHEBI:144078) is a sesquiterpenoid (CHEBI:26658) dihydroartemisinic acid (CHEBI:144078) is conjugate acid of dihydroartemisinate (CHEBI:143905)

Incoming	dihydroartemisinate (CHEBI:143905) is conjugate base of dihydroartemisinic acid (CHEBI:144078)

IUPAC Name

(2R)-2-[(1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]propanoic acid

Synonyms	Sources
(−)-dihydroartemisinic acid	KNApSAcK
(2R)-2-[(1R)-4β,7-Dimethyl-1,2,3,4,4aβ,5,6,8aβ-octahydronaphthalen-1α-yl]propionic acid	ChEBI
dihydroarteannuic acid	MetaCyc
dihydroartemisinic acid	ChEBI

Registry Number	Type	Source
85031-59-0	CAS Registry Number	KNApSAcK

Last Modified

12 July 2019